JP5667744B2 - モノマーでありフェノラートであるポリエーテルケトンの製造方法 - Google Patents
モノマーでありフェノラートであるポリエーテルケトンの製造方法 Download PDFInfo
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- JP5667744B2 JP5667744B2 JP2008286967A JP2008286967A JP5667744B2 JP 5667744 B2 JP5667744 B2 JP 5667744B2 JP 2008286967 A JP2008286967 A JP 2008286967A JP 2008286967 A JP2008286967 A JP 2008286967A JP 5667744 B2 JP5667744 B2 JP 5667744B2
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- Prior art keywords
- polymerization
- chloro
- reaction
- alkali metal
- temperature
- Prior art date
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- 229920001643 poly(ether ketone) Polymers 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title abstract description 34
- 239000000178 monomer Substances 0.000 title description 27
- 150000004707 phenolate Chemical class 0.000 title 1
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 107
- RUETVLNXAGWCDS-UHFFFAOYSA-N (4-chlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RUETVLNXAGWCDS-UHFFFAOYSA-N 0.000 claims abstract description 104
- 238000006243 chemical reaction Methods 0.000 claims abstract description 77
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000002904 solvent Substances 0.000 claims abstract description 34
- 239000002585 base Substances 0.000 claims abstract description 26
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 23
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 60
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 36
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 31
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 6
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 3
- 238000009489 vacuum treatment Methods 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 abstract description 16
- 238000002360 preparation method Methods 0.000 abstract description 4
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 abstract description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012965 benzophenone Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000126 substance Substances 0.000 description 36
- 238000004821 distillation Methods 0.000 description 27
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- 235000017550 sodium carbonate Nutrition 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 12
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000004696 Poly ether ether ketone Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 8
- 229940031826 phenolate Drugs 0.000 description 8
- 229920002530 polyetherether ketone Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- BWQOPMJTQPWHOZ-UHFFFAOYSA-N (2,3-difluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1F BWQOPMJTQPWHOZ-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229940050176 methyl chloride Drugs 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 5
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006172 buffering agent Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002954 polymerization reaction product Substances 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000007790 scraping Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 description 3
- 235000011008 sodium phosphates Nutrition 0.000 description 3
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- FJUZEZRZKVMAMD-DRZCJDIDSA-N (2R,3S)-2-[[(2R)-2-acetamido-3-(3-fluorophenyl)propanoyl]amino]-5-methoxy-4-methoxycarbonyl-3-methyl-5-oxopentanoic acid Chemical compound COC(=O)C(C(=O)OC)[C@H](C)[C@H](C(O)=O)NC(=O)[C@H](NC(C)=O)CC1=CC=CC(F)=C1 FJUZEZRZKVMAMD-DRZCJDIDSA-N 0.000 description 2
- OGTSHGYHILFRHD-UHFFFAOYSA-N (4-fluorophenyl)-phenylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 OGTSHGYHILFRHD-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 description 2
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 229920006015 heat resistant resin Polymers 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- BFFHEHNJSNFLRF-UHFFFAOYSA-N (2-chlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1Cl BFFHEHNJSNFLRF-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XAYKIPCPOCXUBY-UHFFFAOYSA-N 2-[3-(2-hydroxypropyl)pyridin-1-ium-1-yl]acetate Chemical compound CC(O)CC1=CC=C[N+](CC([O-])=O)=C1 XAYKIPCPOCXUBY-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- 150000001501 aryl fluorides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4075—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group from self-polymerisable monomers, e.g. OH-Ar-X
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN571/MUM/2008 | 2008-03-24 | ||
| IN571MU2008 | 2008-03-24 | ||
| EP08251052.0 | 2008-03-25 | ||
| EP08251052A EP2105430B1 (en) | 2008-03-24 | 2008-03-25 | Polyether ketone, its monomer and its phenolate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009227961A JP2009227961A (ja) | 2009-10-08 |
| JP5667744B2 true JP5667744B2 (ja) | 2015-02-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008286967A Active JP5667744B2 (ja) | 2008-03-24 | 2008-11-07 | モノマーでありフェノラートであるポリエーテルケトンの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7879199B2 (zh) |
| EP (1) | EP2105430B1 (zh) |
| JP (1) | JP5667744B2 (zh) |
| KR (1) | KR101562387B1 (zh) |
| CN (1) | CN101544555B (zh) |
| AT (1) | ATE533741T1 (zh) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE533741T1 (de) * | 2008-03-24 | 2011-12-15 | Gharda Chemicals Ltd | Polyetherketon, sein monomer und phenolat |
| WO2010046483A1 (en) * | 2008-10-24 | 2010-04-29 | Solvay Advanced Polymers, L.L.C. | Improved process for preparing a poly(aryl ether ketone) using a high purity 4,4'-difluorobenzophenone |
| JP5760644B2 (ja) * | 2011-04-26 | 2015-08-12 | 東レ株式会社 | 環式ポリフェニレンエーテルエーテルケトン組成物の製造方法 |
| EP2937374B1 (en) * | 2012-12-21 | 2018-06-27 | Toray Industries, Inc. | Method for producing cyclic polyphenylene ether ether ketone composition and linear polyphenylene ether ether ketone, and method for producing polyphenylene ether ether ketone |
| CN103992472B (zh) * | 2014-05-22 | 2016-03-02 | 吉林大学 | 一种聚醚酮树脂及其聚合终止的制备方法 |
| US20160185984A1 (en) * | 2014-12-26 | 2016-06-30 | Dow Global Technologies Llc | Pore-fill compositions |
| CN107936243A (zh) * | 2017-12-07 | 2018-04-20 | 山东凯盛新材料股份有限公司 | 半连续法生产聚醚酮酮的工艺 |
| CN113166396B (zh) * | 2018-06-21 | 2024-05-14 | 索尔维特殊聚合物美国有限责任公司 | 聚(醚酮酮)（pekk）聚合物及复合材料 |
| FR3105230B1 (fr) * | 2019-12-20 | 2021-12-17 | Arkema France | Procédé de fabrication d’un diéther aromatique et procédés correspondants de fabrication de poly-aryl-éther-cétones |
| JP7332837B2 (ja) | 2021-07-30 | 2023-08-23 | ポリプラスチックス株式会社 | 全芳香族エーテルケトン樹脂組成物及びその製造方法、成形品、並びに当該樹脂組成物の溶融粘度の滞留安定性の向上方法 |
| CN113651954A (zh) * | 2021-08-16 | 2021-11-16 | 吉林省中研高分子材料股份有限公司 | 用于合成聚醚醚酮的组合物、聚醚醚酮的合成方法及聚醚醚酮 |
| CN117143331B (zh) * | 2023-11-01 | 2024-01-30 | 江苏亨峰隆新材料有限公司 | 一种超临界二氧化碳精制聚醚酮的方法及生产系统 |
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| US2284124A (en) * | 1939-12-01 | 1942-05-26 | Dow Chemical Co | Purification of high-melting organic compounds |
| US3403183A (en) * | 1966-12-16 | 1968-09-24 | Koppers Co Inc | Production of benzophenones |
| US3850988A (en) * | 1971-09-07 | 1974-11-26 | Gaf Corp | Purification of benzophenones |
| US3819492A (en) * | 1971-11-08 | 1974-06-25 | Cosden Oil & Chem Co | Distillation of aromatic ketone from aromatic alcohol with acid |
| US3953400A (en) * | 1972-01-17 | 1976-04-27 | Raychem Corporation | Polyketones and methods therefor |
| GB8315610D0 (en) * | 1983-06-07 | 1983-07-13 | Ici Plc | Chemical process |
| GB8315612D0 (en) * | 1983-06-07 | 1983-07-13 | Ici Plc | Chemical process |
| US4568429A (en) | 1984-03-02 | 1986-02-04 | Gaf Corporation | Process for the preparation of 2,4-dihydroxybenzophenones |
| GB8413314D0 (en) * | 1984-05-24 | 1984-06-27 | Ici Plc | Purification |
| GB8429609D0 (en) | 1984-11-23 | 1985-01-03 | Ici Plc | Polyketone |
| DE3542481A1 (de) * | 1984-12-11 | 1986-06-19 | Mitsubishi Chemical Industries Ltd., Tokio/Tokyo | Verfahren zur herstellung aromatischer polyketone |
| GB8527756D0 (en) * | 1985-11-11 | 1985-12-18 | Ici Plc | Aromatic polymer & process |
| JPS6327448A (ja) * | 1986-07-17 | 1988-02-05 | Daicel Chem Ind Ltd | 高純度ビスフエノ−ルアルカリ金属二塩の製造方法 |
| US5137988A (en) * | 1986-07-25 | 1992-08-11 | Amoco Corporation | Amino-terminated poly(aryl ether ketones) |
| JPS6465129A (en) | 1987-09-04 | 1989-03-10 | Mitsubishi Gas Chemical Co | Production of aromatic polyether |
| JPH0249748A (ja) * | 1988-05-31 | 1990-02-20 | Mitsubishi Kasei Corp | フェノラートの製造法 |
| EP0344688B1 (en) | 1988-05-31 | 1993-08-04 | Mitsubishi Kasei Corporation | Process for producing a phenolate and process for producing an aromatic polyether ketone employing it |
| JPH0277423A (ja) * | 1988-06-07 | 1990-03-16 | Mitsubishi Kasei Corp | ポリエーテルケトンの製造法 |
| DE69033282T2 (de) * | 1989-05-23 | 1999-12-30 | Teijin Ltd | Poly(arylen-äther-keton), verfahren zur herstellung desselben und dessen verwendung |
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| JPH04363322A (ja) * | 1990-11-05 | 1992-12-16 | Mitsubishi Kasei Corp | 芳香族ポリ（チオ）エーテルケトンの製造法 |
| US5147512A (en) * | 1991-06-28 | 1992-09-15 | Lloyd Berg | Separation of ketone isomers by extractive distillation |
| JPH05178983A (ja) | 1991-12-27 | 1993-07-20 | Mitsubishi Kasei Corp | 芳香族ポリエーテルケトンの製造方法 |
| JPH05178984A (ja) | 1991-12-27 | 1993-07-20 | Mitsubishi Kasei Corp | 芳香族ポリエーテルケトンの製造方法 |
| US5523384A (en) * | 1995-03-28 | 1996-06-04 | E. I. Du Pont De Nemours And Company | Process for preparing polyether ketones |
| GB2364319B (en) * | 2000-07-06 | 2003-01-15 | Gharda Chemicals Ltd | Melt processible polyether ether ketone polymer |
| US7182839B2 (en) * | 2001-08-06 | 2007-02-27 | Baker Hughes Incorporated | Preventing deposition of fouling agents onto equipment |
| WO2005032687A2 (en) * | 2003-09-30 | 2005-04-14 | Clark Arthur F | Method for separating volatile components by dilutive distillation |
| DE102005002084A1 (de) * | 2005-01-14 | 2006-07-20 | Degussa Ag | Verfahren zur Herstellung von Polyarylenetherketonen |
| CN1305935C (zh) * | 2005-03-17 | 2007-03-21 | 吉林大学 | 电活性聚芳醚酮（砜）系列聚合物及其制备方法 |
| EP1903024B1 (en) | 2006-09-04 | 2010-11-24 | Gharda Chemicals Limited | Improved process for the production of poly (ether ketone) - PEK- and its monomer |
| ATE533741T1 (de) * | 2008-03-24 | 2011-12-15 | Gharda Chemicals Ltd | Polyetherketon, sein monomer und phenolat |
-
2008
- 2008-03-25 AT AT08251052T patent/ATE533741T1/de active
- 2008-03-25 EP EP08251052A patent/EP2105430B1/en active Active
- 2008-04-29 US US12/150,511 patent/US7879199B2/en active Active
- 2008-09-04 KR KR1020080087096A patent/KR101562387B1/ko active IP Right Grant
- 2008-09-24 CN CN2008101612781A patent/CN101544555B/zh active Active
- 2008-11-07 JP JP2008286967A patent/JP5667744B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090101794A (ko) | 2009-09-29 |
| CN101544555A (zh) | 2009-09-30 |
| EP2105430A1 (en) | 2009-09-30 |
| US20090240020A1 (en) | 2009-09-24 |
| EP2105430B1 (en) | 2011-11-16 |
| US7879199B2 (en) | 2011-02-01 |
| JP2009227961A (ja) | 2009-10-08 |
| KR101562387B1 (ko) | 2015-10-21 |
| CN101544555B (zh) | 2013-11-06 |
| ATE533741T1 (de) | 2011-12-15 |
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